4-Toluenesulfonyl chloride → HCID 54385761, compound

HRID 1077943Notes

Reaction equation

HRID 1077943 reaction equation
[CH3:1][C:2]([CH2:4][C@@H:5]([C@@H:7]([CH2:9][OH:10])[OH:8])[OH:6])=[O:3].[S:11](Cl)([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12]>N1C=CC=CC=1>[CH3:1][C:2]([CH2:4][C@@H:5]([C@@H:7]([CH2:9][O:10][S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[OH:8])[OH:6])=[O:3]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 53696787HCID 53696787, compound

Product 1

HCID 54385761HCID 54385761, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methyl-2-deoxy-D-ribose (8 g, 54 mmol) was dissolved in pyridine (60 mL). To this solution was added tosylchloride (10.86 g, 57 mmol) over 1 hour at 0° C. After 14 hours at room temperature, the solution was concentrated, quenched with ice water (250 mL), and extracted with ethyl acetate. The extract was washed with saturated NaHCO3, water, dried, filtered, and concentrated. The residue (13.6 g, 83.5% yield) was used directly. NMR

Workup

  1. concentrationthe solution was concentrated
  2. customquenched with ice water (250 mL)
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated NaHCO3, water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-84abdf53fe28476dab0381a334cfd143
Source dataset
uspto-grants-1996_08
Patent number
US05545636

Reaction notes

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